Spiro compound and organic luminescence device using the same

ABSTRACT

Provided are a novel spiro compound, and an organic luminescence device using the spiro compound and having an optical output with an extremely high efficiency and a high luminance, and an extremely high durability. The Spiro compound is represented by the following general formula [I]: 
                         
(wherein R 1 , R 2 , R 3 , and R 4  represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, a cyano group, or a halogen atom, and R 1 , R 2 , R 3 , and R 4  may be identical or different from each other; and Ar 1  and Ar 2  represent a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted condensed polycyclic heterocyclic group, which may be identical or different from each other.)

TECHNICAL FIELD

The present invention relates to a novel organic compound and an organicluminescence device using the same.

BACKGROUND ART

An organic luminescence device is a device where a thin film including afluorescent organic compound or a phosphorescent organic compound issandwiched between an anode and a cathode, an electron and a hole areinjected from the respective electrodes to generate an exciton of thefluorescent compound or the phosphorescent compound, and light which isemitted when the exciton returns to the ground state is utilized.

According to the study of Kodak company in 1987 (Appl. Phys. Lett. 51,913 (1987)), there has been reported a luminescence with approximately1000 cd/m² at an applied voltage of approximately 10 V in a devicehaving a separated-function type two-layer configuration using ITO as ananode, a magnesium-silver alloy as a cathode, an aluminum quinolinolcomplex as an electron-transporting material and a luminescent material,and a triphenyl amine derivative as a hole-transporting material. Therelated patents include U.S. Pat. Nos. 4,539,507, 4,720,432, 4,885,211,and so on.

In addition, it is possible to generate luminescence in the range ofultraviolet to infrared lights by changing the type of the fluorescentorganic compound, and in recent years various types of compounds havebeen studied actively. For instance, it is described in U.S. Pat. Nos.5,151,629, 5,409,783, 5,382,477, Japanese Patent Application Laid-OpenNos. 2-247278, 3-255190, 5-202356, 9-202878, 9-227576, and so on.

In recent years, many studies have been conducted using phosphorescentcompounds as luminescent materials and using energies in tripletexcitation states. A high luminescence efficiency shown by an organicluminescence device using an iridium complex as a luminescent materialhas been reported by a group of the Princeton University (Nature 395,151 (1998)).

Furthermore, in addition to the organic luminescence device using thelow molecular weight material as mentioned above, an organicluminescence device using a conjugate polymer has been reported by agroup of the Cambridge University (Nature, 347, 539 (1990)). In thisreport, luminescence from a single layer is confirmed by the filmformation of polyphenylene vinylene (PPV) using a coating system.

The related patents of the organic luminescence device using theconjugate polymer include U.S. Pat. Nos. 5,247,190, 5,514,878,5,672,678, Japanese Patent Application Laid-Open Nos. 4-145192,5-247460, and so on.

In this way, the recent progress in the organic luminescence device isremarkable, and the characteristics thereof suggest the possibility ofapplications for various purposes, which enable the luminescence devicewith a high luminance, a high-speed response, and a thin and lightweightform.

However, an optical output of higher luminance or higher conversionefficiency is required under the present conditions. In addition, manyproblems still remain to be solved regarding the durability with respectto a change with time due to a long-term usage, deterioration caused byan atmospheric gas including oxygen, moisture, or the like, and so on.Besides, it is not still insufficient for solving problems related tothe needs for luminescences of blue, green, and red having good colorpurity in the case of considering the applications to a full colordisplay and so on.

On the other hand, a spiro compound having a specific stericconfiguration has been attracting attention as an organic functionalmaterial in terms of the specific physical properties of the material(J. Am. Chem. Soc., vol. 110, page 5687, 1988). As an example of using aspiro compound as an organic luminescence device, Japanese PatentApplication Laid-Open No. 7-278537 or the like can be given, but thecharacteristics thereof in being used as a luminescent material or anelectron-transporting material are not sufficient.

DISCLOSURE OF THE INVENTION

An object of the present invention is to provide a novel spiro compound.

Also, another object of the present invention is to provide an organicluminescence device using a specific spiro compound and having anoptical output with an extremely high efficiency and a high luminance.

In addition, another object of the present invention is to provide anorganic luminescence device having an extremely high durability.Furthermore, another object of the present invention is to provide anorganic luminescence device which can be easily and comparativelyinexpensively produced.

Therefore, a spiro compound according to the present invention isrepresented by one of the following general formula [I] and [II]:

(where R₁, R₂, R₃, and R₄ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, a substituted orunsubstituted heterocyclic group, a substituted amino group, a cyanogroup, or a halogen atom, and R₁, R₂, R₃, and R₄ may be identical ordifferent from each other; and Ar₁ and Ar₂ represent a substituted orunsubstituted condensed polycyclic aromatic group or a substituted orunsubstituted condensed polycyclic heterocyclic group, which may beidentical or different from each other); and

(where R₅, R₆, R₇, and R₈ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, a substituted orunsubstituted heterocyclic group, a substituted amino group, a cyanogroup, or a halogen atom, and R₅, R₆, R₇, and R₈ may be identical ordifferent from each other; and Ar₃ and Ar₄ represent a substituted orunsubstituted condensed polycyclic aromatic group or a substituted orunsubstituted condensed polycyclic heterocyclic group, which may beidentical or different from each other.)

Further, an organic luminescence device according to the presentinvention includes at least a pair of electrodes including an anode anda cathode and one or a plurality of layers containing an organiccompound sandwiched between the pair of electrodes, in which at leastone of the layers containing the organic compound preferably contains atleast one spiro compound.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a cross-sectional diagram that illustrates an example of anorganic luminescence device in accordance with the present invention.

FIG. 2 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

FIG. 3 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

FIG. 4 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

FIG. 5 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

FIG. 6 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device in accordance with the presentinvention.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

At first, a spiro compound of the present invention will be described.

The spiro compound of the present invention is represented by the abovegeneral formula [I] or [II].

Here, at least one of Ar₁ and Ar₂, or at least one of Ar₃ and Ar₄ ispreferably a condensed polycyclic aromatic group represented by one ofthe following general formula [III] to [IX]:

(where R₉ represents a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, a cyano group, or a halogen atom; andR₁₀ and R₁₁ represent a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, or a substituted or unsubstitutedheterocyclic group, which may be identical or different from eachother);

(where R₁₂ represents a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, a cyano group, or a halogen atom; andR₁₃ and R₁₄ represent a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, or a substituted or unsubstitutedheterocyclic group, which may be identical or different from eachother); and

(where R₁₅ to R₂₀ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, a substituted orunsubstituted heterocyclic group, a substituted amino group, a cyanogroup, or a halogen atom.)

Specific examples of substituents in the above general formula [I] to[IX] are shown below.

The alkyl group includes a methyl group, an ethyl group, an n-propylgroup, an iso-propyl group, an n-butyl group, a tert-butyl group, anoctyl group, and the like.

The aralkyl group includes a benzyl group, a phenethyl group, and thelike.

The aryl group includes a phenyl group, a biphenyl group, a tert-phenylgroup, and the like.

The heterocyclic group includes a thienyl group, a pyrrolyl group, apyridyl group, an oxazolyl group, an oxadiazolyl group, a thiazolylgroup, a thiadiazolyl group, a tert-thienyl group, and the like.

The substituted amino group includes a dimethylamino group, adiethylamino group, a dibenzylamino group, a diphenylamino group, aditolylamino group, a dianisolylamino group, and the like.

The halogen atom includes fluorine, chlorine, bromine, iodine, and thelike.

The condensed polycyclic aromatic group includes a fluorenyl group, anaphthyl group, a fluoranthenyl group, an anthryl group, a phenanthrylgroup, a pyrenyl group, a tetracenyl group, a pentacenyl group, atriphenylenyl group, a perylenyl group, and the like.

The condensed polycyclic heterocyclic group includes a carbazolyl group,a diazafluorenyl group, an acridinyl group, and the like.

The substituents which the above-mentioned substituents may have includealkyl groups such as a methyl group, an ethyl group, and a propyl group;aralkyl groups such as a benzyl group, and a phenethyl group; arylgroups such as a phenyl group, and a biphenyl group; heterocyclic groupssuch as a thienyl group, a pyrrolyl group, and a pyridyl group; aminogroups such as a dimethylamino group, a diethylamino group, adibenzylamino group, a diphenylamino group, a ditolylamino group, and adianisolylamino group; alkoxyl groups such as a methoxyl group, anethoxyl group, a propoxyl group, and a phenoxyl group; a cyano group;halogen atoms such as fluorine, chlorine, bromine, and iodine; and thelike.

Next, although a typical example of the spiro compound of the presentinvention will be hereinafter given, the present invention is notlimited thereto.

The Spiro compound of the present invention can be synthesized by agenerally well-known method, for example an intermediate of the spirocompound is obtained by a method described in J. Org. Chem., 61, 6906,1996, J. Am. Chem. Soc., 80, 1883, 1958, or the like, and furthermorethe intermediate can be synthesized by the suzuki coupling method (e.g.,Chem. Rev. 1995, 95, 2457-2483) using a palladium catalyst, the Yamamotomethod (e.g., Bull. Chem. Soc. Jpn. 51, 2091, 1978) using a nickelcatalyst, a method in which a synthesis is performed by using a tin arylcompound (e.g., J. Org. Chem., 52, 4296, 1987), and so on.

As compared with the conventional compound, the spiro compound of thepresent invention is a compound having excellent electron-transportingproperty, luminescence property and durability, which is useful fororganic compound-containing layers of an organic luminescence device,particularly an electron-transporting layer and a luminescent layer, anda layer formed by a vacuum evaporation method, a solution-coatingmethod, or the like hardly causes crystallization or the like and isexcellent in stability with time.

Next, the organic luminescence device of the present invention will bedescribed in detail.

The organic luminescence device of the present invention includes atleast a pair of electrodes including an anode and a cathode and one orplural organic compound-containing layers sandwiched between the pair ofelectrodes, in which at least one layer of the organiccompound-containing layers contains at least one spiro compoundrepresented by the above general formula [I] or the general formula[II].

In the organic luminescence device of the present invention, it ispreferable that at least an electron-transporting layer or a luminescentlayer among the organic-compound-containing layers contain at least oneSpiro compound.

In the organic luminescence device of the present invention, the spirocompound represented by the above general formula [I] or the generalformula [II] is formed between the anode and the cathode by the vacuumevaporation method or the solution-coating method. The thickness of theorganic layer is smaller than 10 μm, and it is preferable to make thelayer as a thin film with a thickness of preferably 0.5 μm or less, morepreferably 0.01 to 0.5 μm.

Further, according to a preferable mode of the organic luminescencedevice of the present invention, at least a luminescent layer among thelayers containing the organic compound includes at least one spirocompound and a fluorene compound represented by one of the followinggeneral formula [X] and [XI]:

(where R₂₁ and R₂₂ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group, R₂₁, themselves or R₂₂ themselves,which are bonded to different fluorene groups, may be identical ordifferent from each other, and R₂₁ and R₂₂ that are bonded to the samefluorene group may be identical or different from each other; R₂₃ andR₂₄ represent a hydrogen atom, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a cyano group, or a halogen atom, and R₂₃ themselves or R₂₄themselves, which are bonded to different fluorene groups, may beidentical or different from each other, and R₂₃ and R₂₄ that are bondedto the same fluorene group may be identical or different from eachother; Ar₅, Ar₆, Ar₇, and Ar₈ represent a substituted or unsubstitutedaromatic group, a substituted or unsubstituted heterocyclic group, asubstituted or unsubstituted condensed polycyclic aromatic group, or asubstituted or unsubstituted condensed polycyclic heterocyclic group,which may be identical or different from each other, and Ar₅ and Ar₆ aswell as Ar₇ and Ar₈ may be bonded with each other to form rings,respectively; and n represents an integral number of 1 to 10); and

(where R₂₅ and R₂₆ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group, R₂₅ themselves or R₂₆ themselves,which are bonded to different fluorene groups, may be identical ordifferent from each other, and R₂₅ and R₂₆ that are bonded to the samefluorene group may be identical or different from each other; R₂₇ andR₂₈ represent a hydrogen atom, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a cyano group, or a halogen atom, and R₂₇ themselves or R₂₈themselves, which are bonded to different fluorene groups, may beidentical or different from each other, and R₂₇ and R₂₈ that are bondedto the same fluorene group may be identical or different from eachother; Ar₉ and Ar₁₀ represent a substituted or unsubstituted divalentaromatic group or a substituted or unsubstituted divalent heterocyclicgroup, which may be identical or different from each other; Ar₁₁, Ar₁₂,Ar₁₃, and Ar₁₄ represent a substituted or unsubstituted aromatic group,a substituted or unsubstituted heterocyclic group, a substituted orunsubstituted condensed polycyclic aromatic group, or a substituted orunsubstituted condensed polycyclic heterocyclic group, which may beidentical or different from each other, and Ar₁₁ and Ar₁₂ as well asAr₁₃ and Ar₁₄ may be bonded with each other to form rings, respectively;and m represents an integral number of 1 to 10.)

Specific examples of substituents in the general formula [X] and [XI]are the same as those as in the cases of the above general formula [I]to [IX]. Typical examples of the fluorene compounds represented by thegeneral formula [X] or [XI] will be given thereinafter, but the presentinvention is not limited thereto.

Preferable examples of the organic luminescence device are shown inFIGS. 1 to 6, respectively.

FIG. 1 is a cross-sectional diagram that illustrates an example of theorganic luminescence device of the present invention. In FIG. 1, thedevice comprises an anode 2, a luminescent layer 3, and a cathode 4,which are formed on a substrate 1 in that order. The luminescence deviceused herein is useful when it singly has a hole-transporting ability, anelectron-transporting ability, and a luminescence property in itself orwhen it is used in combination with compounds having thosecharacteristics.

FIG. 2 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device of the present invention. In FIG. 2, thedevice comprises an anode 2, a hole-transporting layer 5, anelectron-transporting layer 6, and a cathode 4, which are formed on asubstrate 1 in that order. In this case, a luminescent material isuseful when a material having one or both of a hole-transportingproperty and an electron-transporting property is used for therespective layers and is used in combination with a hole-transportingmaterial or an electron-transporting material having no luminescenceproperty. In addition, in this case, the luminescent layer 3 is composedof either the hole-transporting layer 5 or the electron-transportinglayer 6.

FIG. 3 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device of the present invention. In FIG. 3, thedevice comprises an anode 2, a hole-transporting layer 5, a luminescentlayer 3, an electron-transporting layer 6, and a cathode 4, which areformed on a substrate 1 in that order. This is one in which acarrier-transporting function and a luminescence function are separatedfrom each other, and is used appropriately in combination with compoundshaving a hole-transporting property, an electron-transporting property,and a luminescence property, respectively. Thus, the degree of freedomin selecting a material increases extremely. In addition, various kindsof compounds having different luminescent wavelengths can be used.Therefore, the diversity of luminescence hue can be allowed.Furthermore, it also becomes possible to increase the luminescenceefficiency by effectively confining each carrier or exciton in themiddle luminescent layer 3.

FIG. 4 is a cross-sectional diagram that illustrates another example ofthe organic luminescence device of the present invention. In FIG. 4, ascompared with the example of FIG. 3, the device is constructed such thata hole-injection layer 7 is inserted in the anode 2 side. It iseffective in the improvement of an adhesion between the anode 2 and thehole-transporting layer 5 or the improvement of an injection property ofholes, so that it is effective in lowering voltage.

FIGS. 5 and 6 are cross-sectional diagrams that illustrate otherexamples of the organic luminescence device of the present invention,respectively. In FIGS. 5 and 6, as compared with the examples of FIGS. 3and 4, the device is constructed such that a layer (a hole-blockinglayer 8) that prevents a hole or an exciton from passing toward thecathode 4 side is inserted between the luminescent layer 3 and theelectron-transporting layer 6. The use of a compound having an extremelyhigh ionization-potential as the hole-blocking layer 8 allows aconfiguration effective to an improvement in luminescence efficiency.

However, in FIGS. 1 to 6, there are shown common basic deviceconfigurations. The configuration of the organic luminescence deviceusing the compound of the present invention is not limited thereto. Forinstance, it is possible to adopt various layer configurations such asone in which an insulating layer is formed at the interface between theelectrode and the organic layer, one in which an adhesive layer or aninterference layer is formed, and one in which the hole-transportinglayer is composed of two layers with different ionization potentials.

The spiro compounds represented by the general formula [I] or thegeneral formula [II] to be used in the present invention are compoundseach having excellent electron-transporting property, luminescenceproperty, and durability as compared with the conventional compounds,and-they can be used in any modes of FIGS. 1 to 6.

In the present invention, the spiro compounds represented by the generalformula [I] or the general formula [II] are used as structuralcomponents of the electron-transporting layer or the luminescent layer.However, hole-transporting compounds, luminescent compounds,electron-transporting compounds, or the like, which have been known, maybe used together if required.

The examples of those compounds will be given below.

Hole-transporting Compound

Electron-transporting Luminescent Material

Luminescent Material

Luminescent Layer Matrix Material and Electron-transporting Material

Polymeric Hole-transporting Material

Polymeric Luminescent Material and Charge-transporting Material

In the organic luminescence device of the present invention, the layercontaining the spiro compound represented by the general formula [I] orthe general formula [II] and the layer containing another organiccompound are generally formed as thin films by a vacuum evaporationmethod, or by a coating method after being dissolved in an appropriatesolvent. In particular, in the case of forming a film with a coatingmethod, the film may be formed in combination with an appropriate binderresin.

The above binder resin can be selected from a wide variety of the binderresins including, for example, polyvinyl carbazole resin, polycarbonateresin, polyester resin, polyarylate resin, polystyrene resin, acrylicresin, methacryl resin, butyral resin, polyvinyl acetal resin, diallylphthalate resin, phenol resin, epoxy resin, silicone resin, polysulfoneresin, and urea resin, although not limited to them. In addition, thoseresins may be used solely or one or more resins may be combined witheach other as a copolymer.

The anode material may be one preferably having a large work function.For example, a simple metal substance such as gold, platinum, nickel,palladium, cobalt, selenium, or vanadium, or an alloy thereof, or ametal oxide such as tin oxide, zinc oxide, indium tin oxide (ITO), orindium zinc oxide can be used. In addition, a conductive polymer such aspolyaniline, polypyrrole, polythiophene, or polyphenylene sulfide can bealso used. Those electrode substances may be used solely or two or moresubstances may be used together.

On the other hand, the cathode material may be one preferably having asmall work function. For example, a simple metal substance such aslithium, sodium, potassium, cesium, calcium, magnesium, aluminum,indium, silver, lead, tin, or chromium, or an alloy of plural substancescan be used. It is also possible to use a metal oxide such as indium tinoxide (ITO). In addition, the cathode may be constructed as a singlelayer or may have a multi-layer configuration.

The substance used in the present invention may be, although notparticularly limited to, a non-transparent substrate such as a metallicsubstrate or a ceramic substrate, or a transparent substrate formed ofglass, quartz, plastic sheets, or the like. In addition, it is alsopossible to control the luminescence color light by using a color filterfilm, a fluorescent color-converting filter film, or a dielectricreflection film as a substrate.

Furthermore, a protective layer or a sealing layer may be formed on theprepared device for preventing the device from contacting with oxygen,moisture, or the like. The protective layer may be a diamond thin film,a film made of an inorganic material such as a metal oxide or a metalnitride, or a polymer film made of a fluorocarbon resin, polyparaxylene,polyethylene, a silicone resin, or a polystyrene resin, or furthermoreit may be a photo-curing resin. Furthermore, it is also possible topackage the device itself with an appropriate sealing resin whilecovering it with a glass, a gas-impermeable film, a metal, or the like.

EXAMPLES

Hereinafter, the present invention will be described more specificallywith examples. However, the present invention is not limited to thoseexamples.

Synthesis Example 1

[Synthesis of Exemplified Compound No. 1]

In a 500-ml three-neck flask, 2.0 g (3.16 mmol) of2,2′-7,7′-tetrabromo-9,9′-spirobifluorene [1]^(*1)), 4.5 g (19.0 mmol)of 9,9-dimethylfluorene-2-boronic acid [2], 140 ml of toluene, and 70 mlof ethanol were added, and an aqueous solution of 25 g of sodiumcarbonate/130 ml of water was dropped thereto with stirring in anitrogen atmosphere at room temperature, followed by the addition of 0.7g (0.63 mmol) of tetrakis (triphenylphosphine) palladium (0). Afterstirring the mixture for 30 minutes at room temperature, the temperatureis allowed to rise to 77° C., followed by stirring for 8 hours. Afterthe reaction, an organic layer was extracted with chloroform and wasthen dried with anhydrous sodium sulfate, followed by purification witha silica gel column (hexane+toluene mixture developing solvent).Consequently, 2.5 g (73% yield) of the exemplified compound No. 1 (whitecrystal) was obtained.

Synthesis Example 2

[Synthesis of Exemplified Compound No. 7]

In a 500-ml three-neck flask, 2.0 g (3.16 mmol) of2,2′-7,7′-tetrabromo-9,9′-spirobifluorene [1], 4.7 g (19.0 mmol) ofpyrene-1-boronic acid [2], 140 ml of toluene, and 70 ml of ethanol wereadded, and an aqueous solution of 25 g of sodium carbonate/130 ml ofwater was dropped with stirring in a nitrogen atmosphere at roomtemperature, followed by the addition of 0.7 g (0.63 mmol) of tetrakis(triphenylphosphine) palladium (0). After stirring the mixture for 30minutes at room temperature, the temperature is allowed to rise to 77°C., followed by stirring for 8 hours. After the reaction, an organiclayer was extracted with chloroform and was then dried with anhydroussodium sulfate, followed by purification with a silica gel column(hexane+toluene mixture developing solvent). Consequently, 2.3 g (65%yield) of the exemplified compound No. 7 (white crystal) was obtained.

Synthesis Example 3

[Synthesis of Exemplified Compound No. 14]

In a 300-ml three-neck flask, 2.0 g (3.16 mmol) of2,2′-7,7′-tetrabromo-9,9′-spirobifluorene [1], 3.2 g (19.0 mmol) ofcarbazole [2], and 150 ml of xylene were added, and 2.0 g (20.9 mmol) oft-butoxy sodium was added thereto with stirring in a nitrogen atmosphereat room temperature, followed by heating the mixture to a temperature of50° C. In this mixture, a 5-ml xylene solution of 0.035 g (0.16 mmol) ofpalladium acetate and 0.032 g (0.16 mmol) of tri-t-butylphosphine wasadded, followed by heating the mixture to 130° C. and stirring for 8hours. After the reaction, an organic layer was extracted withchloroform and was then dried with anhydrous sodium sulfate, followed bypurification with a silica gel column (hexane+toluene mixture developingsolvent). Consequently, 1.7 g (55% yield) of the exemplified compoundNo. 14 (white crystal) was obtained.

Synthesis Example 4

[Synthesis of Exemplified Compound No. 20]

In a 300-ml three-neck flask, 3.0 g (9.02 mmol) of5,5′-spirobi(dibenzosilole) [1]^(*2)) and 100 ml of chloroform wereadded, and then 0.07 g (0.45 mmol) of iron chloride (III) was added withstirring at 0° C., followed by dropping 5.9 g (37.0 mmol) of bromine.After stirring the mixture for 6 hours at room temperature, an organiclayer was extracted with chloroform and was then washed with a sodiumthiosulfate aqueous solution, followed by drying with anhydrous sodiumsulfate. A crystal obtained by distilling off the solvent wasre-crystallized with chloroform, resulting in 4.0 g (69% yield) oftetrabromo-5,5′-spiro(dibenzosilole) [2] (white crystal).

Next, in a 500-ml three-neck flask, 2.0 g (3.09 mmol) of [2], 4.4 g(18.5 mmol) of 9,9-dimethylfluorene-2-boronic acid [3], 140 ml oftoluene, and 70 ml of ethanol were added, and an aqueous solution of 25g of sodium carbonate/130 ml of water was dropped in a nitrogenatmosphere, followed by the addition of 0.5 g (0.43 mmol) of tetrakis(triphenylphosphine) palladium (0). After stirring the mixture for 30minutes at room temperature, the temperature is allowed to rise to 77°C., followed by stirring for 8 hours. After the reaction, an organiclayer was extracted with chloroform and was then dried with anhydroussodium sulfate, followed by purification with a silica gel column(hexane+toluene mixture developing solvent). Consequently, 2.2 g (64%yield) of the exemplified compound No. 20 (white crystal) was obtained.

Example 1

A device having the structure shown in FIG. 2 was prepared.

On a glass substrate as a substrate 1, indium tin oxide (ITO) isdeposited into a film with a thickness of 120 nm by a sputtering methodto obtain an anode 2, so that the substrate thus formed is used as atransparent conductive support substrate. This was sequentiallysubjected to ultrasonic cleanings with acetone and isopropyl alcohol(IPA), and was then washed with IPA by boiling, followed by drying.Furthermore, one subjected to UV/ozone cleaning was used as atransparent conductive support substrate.

On the transparent conductive support substrate, a chloroform solutionof the compound represented by the following structural formula wascoated into a film of 30 nm in thickness by a spin-coating method,resulting in a hole-transporting layer 5.

Furthermore, an electron-transporting layer 6 was formed by forming afilm of 50 nm in thickness from a spiro compound represented by theexemplified compound No. 1 by a vacuum evaporation method. The filmformation was performed under the conditions in which the degree ofvacuum at the time of evaporation was 1.0×10⁻⁴Pa and the film formationrate was 0.2 to 0.3 nm/sec.

A metal layer film of 50 nm in thickness was formed on the above organiclayer as a cathode 4 by using an evaporation material including aluminumand lithium (lithium concentration: 1% by atom) by a vacuum evaporationmethod, and further an aluminum layer of 150 nm in thickness was formedby a vacuum evaporation method. The film formation was performed underthe conditions in which the degree of vacuum at the time of evaporationwas 1.0×10⁻⁴Pa and the film formation rate was 1.0 to 1.2 nm/sec.

Furthermore, the resulting product was covered with a protective glassplate in a nitrogen atmosphere and was then sealed with an acrylic resinadhesive.

When a direct current voltage of 10 V was applied on the device obtainedin this way with an ITO electrode (anode 2) provided as a positiveelectrode and an Al—Li electrode (cathode 4) provided as a negativeelectrode, the current was caused to flow into the device at a currentdensity of 11.5 mA/cm² and blue-colored luminescence at a luminance of3800 cd/m² was observed.

Furthermore, when the current density was kept at 10.0 mA/cm² and thevoltage was applied for 100 hours, an initial luminance of 3500 cd/m²changed to a luminance of 3300 cd/m² after 100 hours, indicating smalldeterioration of luminance.

Examples 2 to 10

Devices were prepared and evaluated in the same way as that of Example1, except that the exemplified compounds shown in Table 1 were used inplace of the exemplified compound No. 1. The results are shown in Table1.

Comparative Examples 1 to 3

Devices were prepared and evaluated in the same way as that of Example1, except that the compounds represented by the following structuralformula were used in place of the exemplified compound No. 1. Theresults are shown in Table 1.

Comparative Compound No. 1

Comparative Compound No. 2

Comparative Compound No. 3

TABLE 1 Initial stage Durability Exemplified Applied Current InitialLuminance after compound voltage Luminance density luminance 100-hourExample No. No. (V) (cd/m²) (mA/cm²) (cd/m²) (cd/m²) Example 1 1 10 380010.0 3500 3300 2 5 10 4500 10.0 4100 3800 3 7 10 3500 10.0 3300 3200 410 10 2900 10.0 2700 2500 5 13 10 3800 10.0 3500 3400 6 16 10 2400 10.02200 1900 7 18 10 2400 10.0 2300 2200 8 21 10 3600 10.0 3500 3300 9 2410 2700 10.0 2600 2200 10  27 10 2300 10.0 2100 2000 ComparativeComparative 1 10 850 10.0 800 550 Example 1 2 Comparative 2 10 700 10.0650 250 3 Comparative 3 10 400 10.0 350 100

Example 11

A device having the structure shown in FIG. 3 was prepared.

In the same manner as in Example 1, a hole-transporting layer 5 wasformed on the transparent conductive support substrate.

Further, a luminescent layer 3 was formed by forming a film of 20 nm inthickness from a spiro compound represented by the exemplified compoundNo. 3 by a vacuum evaporation method. The film formation was performedunder the conditions in which the degree of vacuum at the time ofevaporation was 1.0×10⁻⁴Pa and the film formation rate was 0.2 to 0.3nm/sec.

Furthermore, an electron-transporting layer 6 was formed by forming afilm of 40 nm in thickness from aluminum tris quinolinol by a vacuumevaporation method. The film formation was performed under theconditions in which the degree of vacuum at the time of evaporation was1.0×10⁻⁴Pa and the film formation rate was 0.2 to 0.3 nm/sec.

Next, after forming a cathode 4 in the same manner as in Example 1, theresulting product was sealed.

When a direct current voltage of 8 V was applied on the device obtainedin this way with an ITO electrode (anode 2) provided as a positiveelectrode and an Al—Li electrode (cathode 4) provided as a negativeelectrode, the current was caused to flow into the device at a currentdensity of 12.0 MA/cm² and blue-colored luminescence at a luminance of6700 cd/m² was observed.

Furthermore, when the current density was kept at 10.0 mA/cm² and thevoltage was applied for 100 hours, an initial luminance of 5500 cd/m²changed to a luminance of 5200 cd/m² after 100 hours, indicating smalldeterioration of luminance.

Examples 12 to 20

Devices were prepared and evaluated in the same way as that of Example11, except that the exemplified compounds shown in Table 2 were used inplace of the exemplified compound No. 3. The results are shown in Table2.

Comparative Examples 4 to 6

Devices were prepared and evaluated in the same way as that of Example11, except that the comparative compounds No. 1 to No. 3 were used inplace of the exemplified compound No. 3. The results are shown in Table2.

TABLE 2 Initial stage Durability Exemplified Applied Current InitialLuminance after compound voltage Luminance density luminance 100-hourExample No. No. (V) (cd/m²) (mA/cm²) (cd/m²) (cd/m²) Example 11 3 8 670010.0 5500 5200 12 6 8 6500 10.0 5200 4800 13 8 8 7300 10.0 6000 5700 1411 8 5200 10.0 4400 4100 15 15 8 3900 10.0 3600 3400 16 19 8 5100 10.04200 4000 17 23 8 5600 10.0 4600 4300 18 25 8 3600 10.0 2700 2500 19 268 3800 10.0 2900 2600 20 28 8 5200 10.0 4100 3800 ComparativeComparative 1 8 800 10.0 770 450 Example 4  5 Comparative 2 8 500 10.0400 150  6 Comparative 3 8 1200 10.0 900 300

Example 21

A device having the structure shown in FIG. 3 was prepared.

On a transparent conductive support substrate similar to that in Example1, a chloroform solution of a compound represented by the followingstructural formula was applied into a film of 20 nm in thickness by aspin-coating method, resulting in a hole-transporting layer 5.

Furthermore, the spiro compound represented as the exemplified compoundNo. 7 and the fluorene compound represented as the exemplified compoundNo. FL-1 (weight ratio of 100:1) were deposited into a film with athickness of 20 nm by the vacuum evaporation method to form aluminescent layer 3. The film formation was performed under theconditions in which the degree of vacuum at the time of evaporation was1.0×10⁻⁴Pa and the film formation rate was 0.2 to 0.3 nm/sec.

Furthermore, an electron-transporting layer 6 was formed by forming afilm of 40 nm in thickness from aluminum tris quinolinol by a vacuumevaporation method. The film formation was performed under theconditions in which the degree of vacuum at the time of evaporation was1.0×10⁻⁴Pa and the film formation rate was 0.2 to 0.3 nm/sec.

Next, after forming a cathode 4 in the same manner as in Example 1, theresulting product was sealed.

When a direct current voltage of 8 V was applied on the device obtainedin this way with an ITO electrode (anode 2) provided as a positiveelectrode and an Al—Li electrode (cathode 4) provided as a negativeelectrode, the current was caused to flow into the device at a currentdensity of 13.5 mA/cm² and blue-colored luminescence at a luminance of16000 cd/m² was observed.

Furthermore, when the current density was kept at 10.0 mA/cm² and thevoltage was applied for 100 hours, the initial luminance of 12000 cd/m²changed to a luminance of 9000 cd/m² after 100 hours, indicating smalldeterioration of luminance.

Examples 22 to 53

Devices were prepared and evaluated in the same way as that of Example21, except that the exemplified fluorene compound shown in Table 3 wasused in place of the exemplified fluorene compound No. FL-1. The resultsare shown in Table 3.

Comparative Examples 7 to 9

Devices were prepared and evaluated in the same way as that of Example21, except that the comparative compounds No. 1 to No. 3 were used inplace of the exemplified compound No. 7. The results are shown in Table3.

TABLE 3 Initial stage Durability Exemplified Exemplified Applied CurrentInitial Luminance after compound fluorene voltage Luminance densityluminance 100-hour Example No. No. compound No. (V) (cd/m²) (mA/cm²)(cd/m²) (cd/m²) Example 21 7 FL-1 8 16000 10.0 12000 9000 22 7 FL-2 815000 10.0 12000 8000 23 7 FL-3 8 17000 10.0 14000 10000 24 7 FL-4 812000 10.0 8500 7000 25 7 FL-5 8 9000 10.0 7000 6000 26 7 FL-6 8 1900010.0 14000 11000 27 7 FL-7 8 20000 10.0 14000 12000 28 7 FL-9 8 2200010.0 17000 13000 29 7 FL-10 8 21000 10.0 16000 13000 30 7 FL-12 8 1700010.0 11000 8500 31 7 FL-13 8 13000 10.0 10000 7000 32 7 FL-14 8 1800010.0 16000 14000 33 7 FL-15 8 19000 10.0 16000 14000 34 7 FL-18 8 1900010.0 17000 15000 35 7 FL-21 8 23000 10.0 19000 16000 36 7 FL-24 8 2400010.0 19000 17000 37 7 FL-26 8 9500 10.0 8000 6000 38 7 FL-27 8 1700010.0 13000 11000 39 7 FL-28 8 10000 10.0 8000 6500 40 7 FL-29 8 800010.0 7000 6000 41 7 FL-30 8 9500 10.0 8000 6500 42 7 FL-31 8 12000 10.010000 7000 43 7 FL-32 8 23000 10.0 18000 15000 44 7 FL-33 8 23000 10.017000 14000 45 7 FL-36 8 25000 10.0 19000 16000 46 7 FL-37 8 25000 10.018000 15000 47 7 FL-38 8 20000 10.0 17000 14000 48 7 FL-39 8 24000 10.019000 16000 49 7 FL-41 8 26000 10.0 20000 16000 50 7 FL-42 8 26000 10.021000 17000 51 7 FL-44 8 15000 10.0 12000 9500 52 7 FL-45 8 12000 10.09000 7500 53 7 FL-46 8 13000 10.0 11000 7000 Comparative ComparativeFL-1 8 3000 10.0 2500 900 Example 7 1  8 Comparative FL-1 8 2000 10.01500 200 2  9 Comparative FL-1 8 4500 10.0 3500 600 3

Example 54

A device having the structure shown in FIG. 3 was prepared.

On a transparent conductive support substrate similar to that in Example1, a chloroform solution of a compound represented by the followingstructural formula was applied into a film of 20 nm in thickness by aspin-coating method, resulting in a hole-transporting layer 5.

Furthermore, the spiro compound represented as the exemplified compoundNo. 2 and a compound represented by the following structural formula(weight ratio of 100:5) were deposited into a film with a thickness of20 nm by the vacuum evaporation method to form a luminescent layer 3.The film formation was performed under the conditions in which thedegree of vacuum at the time of evaporation was 1.0×10⁻⁴Pa and the filmformation rate was 0.2 to 0.3 nm/sec.

Furthermore, an electron-transporting layer 6 was formed by forming afilm of 40 nm in thickness from bathophenanthroline (BPhen) by thevacuum evaporation method. The film formation was performed under theconditions in which the degree of vacuum at the time of evaporation was1.0×10⁻⁴Pa and the film formation rate was 0.2 to 0.3 nm/sec.

Next, after forming a cathode 4 in the same manner as in Example 1, theresulting product was sealed.

When a direct current voltage of 8 V was applied on the device obtainedin this way with an ITO electrode (anode 2) provided as a positiveelectrode and an Al—Li electrode (cathode 4) provided as a negativeelectrode, the current was caused to flow into the device at a currentdensity of 10.5 mA/cm² and green-colored luminescence at a luminance of9000 cd/m² was observed.

Furthermore, when the current density was kept at 7.0 mA/cm² and thevoltage was applied for 100 hours, the initial luminance of 7500 cd/m²changed to a luminance of 6500 cd/m² after 100 hours, indicating smalldeterioration of luminance.

Examples 55 to 63

Devices were prepared and evaluated in the same way as that of Example54, except that the exemplified compound shown in Table 4 was used inplace of the exemplified compound No. 2. The results are shown in Table4.

Comparative Examples 10 to 12

Devices were prepared and evaluated in the same way as that of Example54, except that the comparative compounds No. 1 to No. 3 were used inplace of the exemplified compound No. 2. The results are shown in Table4.

TABLE 4 Initial stage Durability Exemplified Applied Initial Luminancecompound voltage Luminance Current density luminance after 100-hourExample No. No. (V) (cd/m²) (mA/cm²) (cd/m²) (cd/m²) Example 54 2 8 90007.0 7500 6500 55 4 8 9500 7.0 8000 6500 56 6 8 7000 7.0 6000 5000 57 128 8000 7.0 6000 5500 58 14 8 14000 7.0 11000 9000 59 15 8 10000 7.0 90007500 60 20 8 10000 7.0 8000 7000 61 22 8 9500 7.0 8000 7500 62 29 815000 7.0 13000 10000 63 30 8 8500 7.0 8000 7000 Comparative Comparative1 8 1300 7.0 900 300 Example 10 11 Comparative 2 8 1000 7.0 900 100 12Comparative 3 8 2500 7.0 2000 700

Example 64

A device having the structure shown in FIG. 1 was prepared.

On a transparent conductive support substrate which was similar to thatof Example 1, a solution prepared by dissolving 0.050 g of a spirocompound represented by the exemplified compound No. 1 and 1.00 g ofpoly-N-vinyl carbazole (a weight average molecular weight=63,000) in 80ml of chloroform was applied into a film of 120 nm in thickness by aspin-coating method (rotation speed=2000 rpm) to form an organic layer(a luminescent layer 3).

Next, after forming a cathode 4 in the same manner as in Example 1, theresulting product was sealed.

When a direct current voltage of 10 V was applied on the device obtainedin this way with an ITO electrode (anode 2) provided as a positiveelectrode and an Al—Li electrode (cathode 4) provided as a negativeelectrode, the current was caused to flow into the device at a currentdensity of 8.0 mA/cm² and blue-colored luminescence at a luminance of1900 cd/m² was observed.

Furthermore, when the current density was kept at 5.0 mA/cm² and thevoltage was applied for 100 hours in the nitrogen atmosphere, theinitial luminance of 1000 cd/m² changed to a luminance of 850 cd/m²after 100 hours, indicating small deterioration of luminance.

Examples 65 to 68

Devices were prepared and evaluated in the same way as that of Example64, except that the exemplified compound shown in Table 5 was used inplace of the exemplified compound No. 1. The results are shown in Table5.

Comparative Examples 13 to 15

Devices were prepared and evaluated in the same way as that of Example64, except that the comparative compounds No. 1 to No. 3 were used inplace of the exemplified compound No. 1. The results are shown in Table5.

TABLE 5 Initial stage Durability Exemplified Applied Current InitialLuminance after 100- compound voltage Luminance density luminance hourExample No. No. (V) (cd/m²) (mA/cm²) (cd/m²) (cd/m²) Example 64 1 101900 5.0 1000 850 65 7 10 2500 5.0 1600 1400 66 19 10 1400 5.0 1000 80067 20 10 1800 5.0 1400 1300 68 24 10 1900 5.0 1200 950 ComparativeComparative 1 10 300 5.0 200 No luminescence Example 13 14 Comparative 210 200 5.0 150 No luminescence 15 Comparative 3 10 550 5.0 400 50

As described with reference to the embodiments and the examples, theorganic luminescence device using the spiro compound represented by thegeneral formula [I] or the general formula [II] provides luminescencewith a high luminance by the application of a low voltage and isexcellent in durability.

In particular, the organic layer containing the spiro compound of thepresent invention is excellent as an electron-transporting layer and isalso excellent as a luminescent layer.

Furthermore, the device can be prepared by using a vacuum evaporationmethod or a casting method, so that the device having a large area canbe easily prepared at a comparatively low cost.

1. An organic luminescence device comprising at least a pair ofelectrodes including an anode and a cathode and one or a plurality oflayers containing an organic compound sandwiched between the pair ofelectrodes, wherein at least one of the layers containing the organiccompound contains at least one spiro compound represented by thefollowing general formula [II]:

wherein R₅, R₆, R₇, and R₈ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, a substituted orunsubstituted heterocyclic group, a substituted amino group, cyanogroup, or a halogen atom, and R₅, R₆, R₇, and R₈, may be identical ordifferent from each other; and Ar₃ and Ar₄ represent a substituted orunsubstituted condensed polycyclic aromatic group or a substituted orunsubstituted condensed polycyclic heterocyclic group, which may beidentical or different from each other and wherein at least one of Ar₃and Ar₄ is a condensed polycyclic aromatic group represented by one ofthe following general formula [III] to [VIII]:

wherein R₉ represents a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, a cyano group, or a halogen atom; andR₁₀ and R₁₁ represent a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, or a substituted or unsubstitutedheterocyclic group, which may be identical or different from each other;

wherein R₁₂ represents a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, a cyano group, or a halogen atom; andR₁₃ and R₁₄ represent a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, or a substituted or unsubstitutedheterocyclic group, which may be identical or different from each other;and

wherein R₁₅ to R₁₈ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, a substituted orunsubstituted heterocyclic group, a substituted amino group, a cyanogroup, or a halogen atom; and wherein at least a luminescent layer amongthe layers containing the organic compound contains at least one of thespiro compounds and a fluorene compound represented by the followinggeneral formula [X]:

wherein R₂₁ and R₂₂ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group, R₂₁ themselves or R₂₂ themselves,which are bonded to different fluorene groups, may be identical ordifferent from each other, and R₂₁ and R₂₂ that are bonded to the samefluorene group may be identical or different from each other; R₂₃ andR₂₄ represent a hydrogen atom, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a cyano group, or a halogen atom, and R₂₃ themselves or R₂₄themselves, which are bonded to different fluorene groups, may beidentical or different from each other, and R₂₃ and R₂₄ that are bondedto the same fluorene group may be identical or different from eachother; Ar₅, Ar₆, Ar₇, and Ar₈ represent a substituted or unsubstitutedaromatic group, a substituted or unsubstituted heterocyclic group, asubstituted or unsubstituted condensed polycyclic aromatic group, or asubstituted or unsubstituted condensed polycyclic heterocyclic group,which may be identical or different from each other, and Ar₅ and Ar₆ aswell as Ar₇ and Ar₈ may be bonded with each other to form rings,respectively; and n represents an integral number of 1 to
 10. 2. Anorganic luminescence device comprising at least a pair of electrodesincluding an anode and a cathode and one or a plurality of layerscontaining an organic compound sandwiched between the pair ofelectrodes, wherein at least one of the layers containing the organiccompound contains at least one spiro compound represented by thefollowing general formula [II]:

wherein R₅, R₆, R₇, and R₈ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, a substituted orunsubstituted heterocyclic group, a substituted amino group, cyanogroup, or a halogen atom, and R₅, R₆, R₇, and R₈ may be identical ordifferent from each other; and Ar₃ and Ar₄ represent a substituted orunsubstituted condensed polycyclic aromatic group or a substituted orunsubstituted condensed polycyclic heterocyclic group, which may beidentical or different from each other and wherein at least one of Ar₃and Ar₄ is a condensed polycyclic aromatic group represented by one ofthe following general formula [III] to [VIII]:

wherein R₉ represents a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, a cyano group, or a halogen atom; andR₁₀ and R₁₁ represent a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, or a substituted or unsubstitutedheterocyclic group, which may be identical or different from each other;

wherein R₁₂ represents a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted amino group, a cyano group, or a halogen atom; andR₁₃ and R₁₄ represent a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aralkyl group, a substitutedor unsubstituted aryl group, or a substituted or unsubstitutedheterocyclic group, which may be identical or different from each other;and

wherein R₁₅ to R₁₈ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, a substituted orunsubstituted heterocyclic group, a substituted amino group, a cyanogroup, or a halogen atom; and wherein at least a luminescent layer amongthe layers containing the organic compound contains at least one of thespiro compounds and a fluorene compound represented by the followinggeneral formula [XI]:

(wherein R₂₅ and R₂₆ represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group, R₂₅ themselves or R₂₆ themselves,which are bonded to different fluorene groups, may be identical ordifferent from each other, and R₂₅ and R₂₆ that are bonded to the samefluorene group may be identical or different from each other; R₂₇ andR₂₈ represent a hydrogen atom, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a cyano group, or a halogen atom, and R₂₇ themselves or R₂₈themselves, which are bonded to different fluorene groups, may beidentical or different from each other, and R₂₇ and R₂₈ that are bondedto the same fluorene group may be identical or different from eachother; Ar₉ and Ar₁₀ represent a substituted or unsubstituted divalentaromatic group or a substituted or unsubstituted divalent heterocyclicgroup, which may be identical or different from each other; Ar₁₁, Ar₁₂,Ar₁₃, and Ar₁₄ represent a substituted or unsubstituted aromatic group,a substituted or unsubstituted heterocyclic group, a substituted orunsubstituted condensed polycyclic aromatic group, or a substituted orunsubstituted condensed polycyclic heterocyclic group, which may beidentical or different from each other, and Ar₁₁ and Ar₁₂ as well asAr₁₃ and Ar₁₄ may be bonded with each other to form rings, respecdvely;and m represents an integral number of 1 to 10.)